High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

Ngong Kodiah Beyeh; Isabel Díez; S Maryamdokht Taimoory; Daniel Meister; Andrew I Feig; John F Trant; Robin H A Ras; Kari Rissanen

doi:10.1039/c7sc05167k

High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

Chem Sci. 2017 Dec 19;9(5):1358-1367. doi: 10.1039/c7sc05167k. eCollection 2018 Feb 7.

Authors

Ngong Kodiah Beyeh^{1

2}, Isabel Díez¹, S Maryamdokht Taimoory², Daniel Meister², Andrew I Feig³, John F Trant², Robin H A Ras^{1

4}, Kari Rissanen⁵

Affiliations

¹ Aalto University , School of Science , Department of Applied Physics , Puumiehenkuja 2 , FI-02150 , Espoo , Finland . Email: tbeyeh@gmail.com ; Email: robin.ras@aalto.fi.
² University of Windsor , Department of Chemistry and Biochemistry , Windsor , ON N9B 3P4 , Canada . Email: j.trant@uwindsor.ca.
³ Wayne State University , Department of Chemistry , 5101 Cass Ave. , Detroit , MI 48202 , USA.
⁴ Aalto University , School of Chemical Engineering , Department of Bioproducts and Biosystems , Kemistintie 1 , 02150 Espoo , Finland.
⁵ University of Jyvaskyla , Department of Chemistry , P. O. Box 35 , FI-40014 Jyväskylä , Finland . Email: kari.t.rissanen@jyu.fi.

Abstract

Pyrophosphate (PPi) is a byproduct of DNA and RNA synthesis, and abnormal levels are indicative of disease. We report the high-affinity binding of PPi in water by N-alkyl ammonium resorcinarene chloride receptors. Experimental analysis using ¹H and ³¹P NMR, isothermal titration calorimetry, mass spectrometry, and UV-vis spectroscopy all support exceptional selectivity of these systems for PPi in water. The measured affinity of K₁ = 1.60 × 10⁷ M^-1 for PPi is three orders of magnitude larger than that observed for binding to another phosphate, ATP. This exceptional anion-binding affinity in water is explored through a detailed density functional theory computational study. These systems provide a promising avenue for the development of future innovative medical diagnostic tools.